The series premiered on June 1, 1998. The title of the show was originally Road Rules: All Stars before it was renamed Real World/Road Rules Challenge by the show's 2nd season, then later abridged to simply The Challenge by the show's 19th season. The series initially used no hosts but instead a former cast member who had been kicked off his or her season, providing assignments as "Mr." or "Ms. Big" (David "Puck" Rainey, David Edwards, and Gladys Sanabria served this role). Later on, however, the series began using hosts: Eric Nies and Mark Long co-hosted a season, and Jonny Moseley and Dave Mirra hosted various seasons before T. J. Lavin became the show's regular host by the 11th season.

The Challenge casts are season specific as the cast varies from season to season. The casts can only be made up of A.) contestants originating from one of The Challenge's related TV programs or B.) contestants originating from one of the few Challenge seasons that have allowed previously unknown contestants. These shows and seasons are: The Challenge's two precursor programs, The Real World and Road Rules, the reality show Are You the One?, The Challenge's spin-off television program, Spring Break Challenge, and The Challenge's own Fresh Meat seasons (only the seasons Fresh Meat, and Fresh Meat II).

A season's typical multitude of cast members are usually divided up into separate teams according to a certain criteria, which varies from season to season. The criteria that teams have been arranged by over the show's history have ranged all across the board, from gender of the contestants and original show of contestants to bad guy/good guy status of contestants and ex-romantic partners of contestants. Each of the opposing teams compete in numerous missions in order to win prizes and advance in the overall game. Following each mission, a team or a cast member is voted into an elimination round to take on the least successful team from the previous mission. In elimination rounds, they must compete against one another to determine which one is eliminated from the season. Each season has its own, very distinct elimination round, distinguished from those of other seasons in title, design, and general atmosphere. Determining which two teams or two cast members are sent into the episode's elimination round frequently leads to drama and contestants playing the game dirty; this is due to the show's contestants being in charge of who is thrown into elimination rounds.[5] Like that of The Real World, sporadically throughout the course of each episode, various contestants are seen privately expressing themselves through reality TV confessionals about the events taking place on the show.

Some seasons, however, have used entirely different formats from the typical: The Island is one Challenge in particular that adopted many features atypical to Real World/Road Rules Challenge, instead taking concepts like that of another reality television game show Survivor; as another example, the first season (Road Rules: All Stars) ironically only included contestants from The Real World and consisted of a much smaller cast before the show was completely reconstructed by its second season. Except for season one, a monetary prize has always been the award for winning the final mission.

Battle of the Sexes and Battle of the Sexes 2: As the title implies, players are divided by gender. Each mission gave points based on finish, either with a partner or individually. After each mission, the players with the most points cumulative from each team became the "Inner Circle" and voted off whoever they wanted to. The winner of each challenge would earn a "lifesaver" which could be given to a member of either team; the recipient of the "lifesaver" would enjoy total immunity from being voted out, which created many interesting situations. No life-shields were used in the second installment. The final three players of each gender would compete against each other in a final race.

Inferno, Inferno II and Inferno 3: Two teams of "Bad Asses" and "Good Guys" (though the original Inferno was Real World vs. Road Rules). Teams nominate two of their own players for each elimination round and vote one of the opponents' two nominations into the "Inferno" round. The players going into the "Inferno" then have the opportunity to save themselves from going in by winning a "life saver" in the challenge before the "Inferno."

Gauntlet, Gauntlet 2 and Gauntlet III: Two teams of "Veterans" and "Rookies" (though the original Gauntlet was Real World vs. Road Rules). In this particular challenge, "Veterans" are considered plays who have participated in a minimum of two challenges. "Rookies" on the other hand had either participated in one challenges or none at all. Team Captains are assigned on a pre-challenge mission. The losing team's captains would alternate between male and female to go into the "Gauntlet," in which they would face off against someone from their own team as voted by the remaining team members.

Fresh Meat and Fresh Meat II: These seasons introduce new people to Challenges without appearing on The Real World or Road Rules. These new players are "drafted" by "alumni" of the opposite gender (those who come from RW, RR, or previous 'FM', some of whom have not been on a Challenge before) to create pairings which are the teams for these Challenges. The winning team chooses one team for an elimination round called an "Exile," while the other team is selected by a vote.

The Duel and The Duel II: Promoted as "every man for himself" as there are no permanent teams (though some individual challenges require teams to be formed). All players compete individually, leading to just one champion of each gender.

The Island: A challenge with no missions, just elimination rounds where the competitors are put on an island with limited supplies. In each episode, the competitors select three people (not necessarily by gender) to go into an elimination round to win safety and a key to the prize money chest at the final challenge. The two non-winning players have a chance to plead their case to all the other competitors at the vote-off, where one player wins a key and the other is eliminated.

The Ruins: Two teams of "Challengers" and "Champions" based on whether players have won a previous season's final challenge. Prior to each challenge, each team nominates a group of three players of each gender within the team for elimination; after that challenge, the winning team's nominated group picks the match-ups for the "Ruins," which consist of a male Challenger against a male Champion, and a female Challenger against a female Champion.

Cutthroat: Teams are not initially set. There is a race in the beginning, and while the top three players are announced, the bottom three are named as captains of the three teams; the three teams are then drafted by the captains (while maintaining equal numbers of players of each gender). Each challenge involves all three teams; the winning team is safe from the elimination round — the "Gulag," while the losing teams go against each other in the Gulag. Voting is done within one's own team by secret ballot to choose one player of each gender to go into the Gulag.

Rivals and Rivals II: Two-player teams of the same gender consist of players who are paired against their "worst enemies," whom they have engaged in bitter feuds, fights and rivalries with in previous Real World and/or Challenge seasons. The challenge winner is safe from elimination – "The Jungle," while the last-place finisher and a non-winning team of the same gender battle it out in "The Jungle." Each challenge alternates between a male and a female Jungle elimination.

Battle of the Exes and Battle of the Exes II: Thirteen teams of ex couples compete in a challenge where the winner is safe from elimination and will be known as "The Power Couple," and they are responsible for choosing one team to go into the elimination round called "The Dome," along with the team that came in last-place in the challenge. A twist was added on Battle of the Exes II: Eliminated teams would compete in "Battle of the Ex-iled," which no one in the house knows about. The eliminated team will compete against the last "Ex-ile" winner and the loser would be permanently eliminated. This lasts until only four teams remain in the house, and the last team standing from Ex-ile will go back to the house for two more challenges before the final, which they are eligible for as long as they are not eliminated again.

Battle of the Seasons (2012): Each team consists of two men and two women from select seasons. After each challenge, there is a winning team and a losing team. The losing team is automatically sent to "The Arena," and faces possible elimination. The winning team become the Power Team, and selects one team to battle against the last-place team in the Arena. The teams entering the Arena must select one player of each gender from their own team to compete in the elimination. If the teams entering the Arena cannot decide which players will compete in the elimination, the Power Team chooses for them. The winning pair in the elimination rounds return to their season and stay in the game, while the losing pair is eliminated, reducing their season to two players.

Free Agents: Each challenge is declared as either an individual, pair, or team challenge. For pair and team challenges, names are drawn out of a bag — one of each gender, or more for multi-team or pair challenges — that will be designated as captains. For team challenges, the captains will select players that will be split evenly amongst gender. For pair challenges, the captains will either select players of the opposite gender for challenges that are designated as male/female pairs, or the same gender for challenges that are designated as same-gender pairs.The winning team/pair/players are safe from elimination, and choose one player of each gender for elimination. The remaining non-winning players then participate in "The Draw," where the one player of each gender that draws a "kill card" faces the previously voted players in the elimination round.

After All Stars, producers decided to include former castmembers of Road Rules in the series as well. In the next season, two six-member teams were sent around the world in a competition to see which show could best the other in head-to-head competition. The series followed the format for three years and brought in hugely successful ratings.

Following the hugely successful boom of reality television in the new millennium, producers decided to add new elements to the series. In 2001, production began on Battle of the Seasons. This season, the first to depart from the previous six-member structure, brought in a large group of former cast members to compete in one location. Beginning with the first Battle of the Seasons, MTV added a fantasy challenge game to their website. Players "draft" cast members, a la fantasy baseball and cast members are given points for performing certain tasks, such as cursing or "hooking up."

After switching to the "vote off" format, the series would alternate between "Battle" seasons, including two seasons of Battle of the Sexes and themed Challenges which included the Gauntlet and Inferno seasons. Both the Gauntlet and Inferno seasons contained "showdown" matches between members of the two opposing teams. The cast member who lost the showdown would be sent home. The Gauntlet seasons featured an intra-cast dynamic as teams were forced to vote off cast members within their own groups into the showdown, while the Inferno seasons featured an inter-cast dynamic as teams were forced to vote off cast members from the other group into the showdown.

In 2005, Bunim-Murray Productions decided to invite new people to the Challenges who were never a part of either Real World or Road Rules and called them 'Fresh Meat.' This decision was forced, in part, because of the status of Road Rules at the time. While Road Rules had stopped production until further notice after its thirteenth season, Real World had just finished wrapping its sixteenth season in Austin, Texas. Road Rules had a fourteenth, and final, season in 2007. One additional 'Fresh Meat' season has followed with cast also being integrated in The Challenge from the 2010 Spring Break Challenge miniseries and Are You the One?[6]

While internal episodes are the usual and feature an original mission, voting process, elimination round, and surrounding social lives between the season's contestants, external episodes feature the season's contestants reviewing themselves in internal episodes and adding feedback. This is typically combined with video clips from the internal episodes in question. The Challenge has three types of these external episodes, an aftershow that takes place sporadically in the form of a series throughout the entire season, a post-show reunion of notable cast members from that season, and a bonus footage special.

Two commonly used terms on the show are "veterans" (or vets) and "rookies." Veterans are particularly thought of as players that have won at least one Challenge season, but the term has also been applied to players who have appeared on several seasons of the show, or have appeared in the final stages of a challenge. Rookies are thought of as players that have done none of the above. The most vulnerable rookies are those who have just recently completed their season on The Real World or Road Rules and are participating in the game for their very first time; often they are the first to be singled out and targeted by everyone else due to their lack of bonds with existing cast. However, at least one rookie has reached the final challenge on every season, for the exceptions of The Island, Fresh Meat II and Battle of the Exes.

Another commonly used term on the show is "alliance." The term is used to refer to challengers working together. These contestants have colluded together so as to increase their overall chances of winning the season game. But for safety in numbers offered by the collusion, the show's contestants would run the risk of victimization to the game's politics and popularity factors. Politics plays a role due to the show's formats in which options of who is thrown into elimination rounds and other determining factors are left up to challengers themselves. Alliances are typically formed through pacts and negotiations made among certain contestants early on in the game. Alliance operations can range from saving alliance members, throwing missions for the purposes of advancing the alliance, picking and choosing based upon alliance involvement as opposed to levels of performance, etc.

In early seasons of the show, alliances were heavily frowned upon by most of the contestants. As such, alliances used to be carried out with much more secrecy, craft, and deviousness. In fact, many of the earliest alliances on the show were formed to sabotage members of one's own team who were perceived as weak. Once exposed, alliances typically came as offensive and shocking to those not involved. Since the later seasons, however, alliances have become a norm among the show's contestants, so much so that most contestants are expected to join an alliance upon beginning out a season. Despite its use among most, there are still a minority of contestants who elect to play the game straightforwardly, feeling as though alliance tactics are a sign of weakness and a lack of competitive spirit. Those who reject alliances, however, are seen as not playing the game strategically. Although the widespread and overt practice of alliance construction has expelled its original devious reputation, its effectiveness and capacity to surprise attack has waned.

Coined in The Challenge: Battle of the Exes II, a "layup" is a metaphorical usage referring to efforts made to ensure that a season's weakest contestant or team or at least highly weakest contestant or team makes it to the final mission. In this sense, a weak contestant/team is given a free ticket to the final mission by most or all of a season's cast. The logic behind this method is that competing against a weaker contestant/team in the final mission creates for a more sure-fire win with least amount of effort as possible. The move is performed by contestants/teams refraining from voting weak links into elimination rounds.

In the The Challenge: Battle of the Exes II Reunion, all the contestants understood the usage, citing Wes Bergmann as the creator. The term was then explained by Wes in description of how the show's cast was making efforts to save Jay Gotti and Jenna Compono for the final, the two viewed as the weakest team of that season.

The Challenge has been shot in many different countries around the world, as well as some taking place in the United States.
During seasons 1, 4, 21, 22, 23 and 25, the cast traveled between several different countries.